Construction of C–O bond via cross-dehydrogenative coupling of sp [3] C–H bond with phenols catalyzed by copper porphyrin

Copper porphyrin-catalyzed construction of ether bond by cross-dehydrogenative coupling of sp [3] C–H bond with phenols bearing electron-withdrawing groups (EWG) was described for the first time. A broad range of substrates afforded different acetals in moderate to excellent yields with good functio...

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Bibliographic Details
Published in:Tetrahedron 2020-11, Vol.76 (45), p.131569, Article 131569
Main Authors: Yang, Shuang, Xiong, Ming-Feng, Tian, Wan-Qun, Zhang, Hao, Xiao, Xin-Yan, Liu, Hai-Yang, Chang, Chi-Kwong
Format: Article
Language:English
Subjects:
Copper
Cross-dehydrogenative coupling
Phenolic etherification
Porphyrin
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Summary:Copper porphyrin-catalyzed construction of ether bond by cross-dehydrogenative coupling of sp [3] C–H bond with phenols bearing electron-withdrawing groups (EWG) was described for the first time. A broad range of substrates afforded different acetals in moderate to excellent yields with good functional group tolerance. The developed method is not only suitable for phenol substrates with ortho-directing groups, but also suitable for those phenol without ortho-directing groups. Significantly, a high turnover number (TON) up to 7300 was achieved in gram-level test. [Display omitted] •Copper porphyrin-catalyzed construction of C-O bond by coupling of cyclic ether with phenols was described firstly.•The reaction greatly extended the phenol substrate scope for construction of C-O bonds.•The reaction achieved a high turnover number (TON) up to 7300 in gram-level test.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131569